Literature DB >> 12049512

Solution-phase hexasaccharide synthesis using glucosyl iodides.

Son N Lam1, Jacquelyn Gervay-Hague.   

Abstract

[reaction: see text] Oligosaccharides composed of 1,6-glucosyl residues have been prepared from glucosyl iodides. The reactions are highly stereoselective, giving the alpha-glycosides as the only isolated products in yields ranging from 84% to 94%. Oligomer synthesis can take place in an iterative 1 + 1 + 1 fashion or in a convergent manner where dimer iodides serve as donors for higher order acceptors.

Entities:  

Year:  2002        PMID: 12049512     DOI: 10.1021/ol025887d

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

2.  Two-step synthesis of the immunogenic bacterial glycolipid BbGL1.

Authors:  Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2008-09-18       Impact factor: 6.005

3.  Regioselective silyl/acetate exchange of disaccharides yields advanced glycosyl donor and acceptor precursors.

Authors:  Hsiao-Wu Hsieh; Matthew W Schombs; Mark A Witschi; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2013-09-17       Impact factor: 4.354

Review 4.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

5.  Integrating ReSET with glycosyl iodide glycosylation in step-economy syntheses of tumor-associated carbohydrate antigens and immunogenic glycolipids.

Authors:  Hsiao-Wu Hsieh; Matthew W Schombs; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2014-02-07       Impact factor: 4.354

6.  Reagent Controlled Stereoselective Synthesis of α-Glucans.

Authors:  Liming Wang; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

  6 in total

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